This invention relates to novel ketone pyrazole, thiophene, and pyridine sulfonylurea herbicidal compounds, agriculturally suitable compositions thereof and a method of using them to control the growth of undesired vegetation.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel shortage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years. A multitude of structural variations exist within the class of herbicides, but they generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings.
EP-A95,925 which was published 12/7/83 discloses herbicidal sulfonylureas of formula ##STR1## wherein
Q is, in part, ##STR2##
R.sub.10 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CO.sub.2 R.sub.24, SO.sub.2 NR.sub.20 R.sub.21 or SO.sub.2 R.sub.22 ;
R.sub.11 is H, C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, OR.sub.16, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; provided that when R.sub.10 is other than C.sub.1 -C.sub.3 alkyl, then R.sub.11 is H, Cl, OCH.sub.3, NO.sub.2, or CH.sub.3 ;
R.sub.12 is H or CH.sub.3 ;
R.sub.13 and R.sub.14 are independently H, C.sub.1 -C.sub.3 alkyl, OR.sub.16, F, Cl, Br, NO.sub.2, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; provided that, when either of R.sub.13 or R.sub.14 is CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21, then the other is H, Cl, CH.sub.3, OCH.sub.3 or NO.sub.2 ; and
R.sub.15 is H or CH.sub.3.
EP-A-87,780 (published 9/7/83) discloses herbicidal sulfonylureas of formula ##STR3## wherein
A is H, C.sub.1 -C.sub.8 alkyl or optionally substituted phenyl;
B and C are independently H, halogen, NO.sub.2, C.sub.1 -C.sub.8 alkyl, arylalkyl, C.sub.1 -C.sub.8 alkoxy, haloalkyl, CO.sub.2 R, CONR.sub.1 R.sub.2, S(O).sub.n R.sub.3, SO.sub.2 NR.sub.4 R.sub.5, or optionally substituted phenyl.
ZA 83/3850 (published 11/28/83) discloses compounds of formula ##STR4## wherein Q is a five-membered, heterocyclic radical which is bound by way of a carbon atom and contains 2 or 3 heteroatoms and which may be optionally substituted by halogen, pseudohalogen, nitro, alkyl, hydroxyl, haloalkyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkylcarbonyl, alkoxycarbonyl, alkoxyalkyl, alkylthiocarbonyl, carbamoyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfinyl, alkylsulfonyl, alkenyloxy or alkynyloxy; and groups such as phenyl, phenoxy or phenylthio, which are unsubstituted or substituted by halogen, nitro, cyano, alkyl, alkoxy, haloalkyl, alkylcarbonyl, alkoxycarbonyl or haloalkoxy; and also benzyl unsubstituted or substituted by halogen and/or alkyl.
U.S. Pat. No. 4,127,405 and U.S. Pat. No. 4,169,719 disclose herbicidal thiophenesulfonamides, wherein the thiophene ring may be optionally substituted with CH.sub.3, Cl or Br.
U.S. Pat. No. 4,398,939 discloses herbicidal thiophenesulfonamides, wherein the thiophene ring is substituted with substituent groups selected from C.sub.1 -C.sub.4 alkyl, C.sub.3 alkenyl, OCH.sub.3, NO.sub.2, Cl, Br, SO.sub.2 N(C.sub.1 -C.sub.3 alkyl).sub.2 or SO.sub.2 N(OCH.sub.3)CH.sub.3.
U.S. Pat. No. 4,481,029 discloses herbicidal thiophenesulfonamides, wherein the thiophene ring is substituted with carboxylic acid, carboxylic ester and alkylcarbonyl groups or derivatives thereof.
U.S. Pat. No. 4,441,910 discloses herbicidal thiophenesulfonamides, wherein the thiophene ring is substituted with the group represented by R.sub.6 S(O).sub.n wherein R.sub.6 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, cyclopentyl or cyclopropylmethyl.
European Publication No. 13,480 (published July 23, 1980) discloses herbicidal pyridine-2-, -3- and -4-sulfonylureas, wherein the pyridine ring may be substituted by Cl, Br, F, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, NO.sub.2 or a carboxylic ester group.
U.S. Pat. No. 4,456,489 (issued 6/29/84) discloses herbicidal pyridine-3-sulfonylureas substituted by C.sub.1 -C.sub.6 alkyl-, C.sub.3 -C.sub.6 alkenyl-, C.sub.2 -C.sub.4 alkoxyalkyl- and C.sub.5 -C.sub.6 cycloalkylsulfonyl groups.
U.S. Pat. No. 4,518,776 (Swiss priority 7/19/82) discloses, in part, a process for the preparation of compounds of formula ##STR5## wherein
G is ##STR6##
R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, halogen, NO.sub.2, CN, NH.sub.2, S(O).sub.n C.sub.1 -C.sub.4 alkyl, SO.sub.2 C.sub.1 -C.sub.4 alkoxy, SO.sub.2 -di-C.sub.1 -C.sub.4 alkylamino, CHO, CONH.sub.2, DC.sub.3 -C.sub.5 alkynyl, CODC.sub.3 -C.sub.5 alkynyl, DC.sub.1 -C.sub.4 alkyl, DC.sub.3 -C.sub.5 alkenyl, COC.sub.1 -C.sub.4 alkyl, CODC.sub.1 -C.sub.4 alkyl or CODC.sub.3 -C.sub.5 alkenyl;
n is 1 or 2;
D is O, S, NH or NC.sub.1 -C.sub.4 alkyl;
R.sub.2 is H, halogen, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; and
A is O, S, NR.sub.5 or --C.dbd.N--.
U.S. Pat. No. 4,521,597 discloses, in part, a process for the preparation of compounds of formula ##STR7## wherein
A is ##STR8##
R.sub.3 is H, halogen, NO.sub.2, OCH.sub.3 or CF.sub.3 ;
R.sub.5 is H, F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, CF.sub.3, S(O).sub.m C.sub.1 -C.sub.5 alkyl, COR.sub.7 or SO.sub.2 NR.sub.8 R.sub.9 ;
Y is O, S, or C(R.sub.6).dbd.N; and
R.sub.7 is H, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 haloalkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 haloalkoxy, C.sub.2 -C.sub.10 alkoxyalkoxy, C.sub.3 -C.sub.5 alkenyloxy, C.sub.3 -C.sub.5 alkynyloxy, phenoxy, benzyloxy, C.sub.1 -C.sub.5 alkylthio or NR.sub.8 R.sub.9.
U.S. Pat. No. 4,549,898 discloses herbicidal sulfonylureas of formula ##STR9## wherein
X is O, S, NR.sub.4 or C(R.sub.5).dbd.N;
Y is O or S;
Z is O or S;
E is N or CH;
R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.1 -C.sub.4 alkylthio, NR.sub.6 R.sub.7 or alkoxyalkyl containing not more than 4 carbon atoms;
R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, C(W)R.sub.8, SO.sub.2 NR.sub.6 R.sub.7, S(O).sub.n C.sub.1 -C.sub.3 alkyl or COR.sub.9 ;
R.sub.3 is H, halogen, C.sub.1 -C.sub.3 alkyl, OCH.sub.3 or CF.sub.3 ;
R.sub.5 is H, NO.sub.2, F, Cl, Br, CH.sub.3, CF.sub.3, S(O).sub.n C.sub.1 -C.sub.3 alkyl, COC.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.3 alkoxy;
R.sub.8 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or alkoxyalkyl containing not more than 4 carbon atoms; and
W is O or NOR.sub.10.
Japanese Patent Application No. 58-70407 (SHO 59-219,218, laid open 12/10/84) discloses pyrazole-5-sulfonylureas of formula ##STR10## wherein
A is H, lower alkyl or phenyl;
B is H or lower alkyl;
D is H, CO.sub.2 R or COAr, halogen, NO.sub.2 or SO.sub.2 NR.sup.1 R.sup.2 ; and
Ar is phenyl optionally substituted with halogen.
U.S. Pat. No. 4,370,480 discloses herbicidal sulfonylureas of formula ##STR11## wherein
R.sub.1 is ##STR12##
R is H, C.sub.1 -C.sub.2 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl; C.sub.1 -C.sub.4 alkyl substituted with one to four substituents selected from 0-3 F, 0-3 Cl, 0-3 Br, 0-2 OCH.sub.3, 0-1 cyano, 0-1 CO.sub.2 R.sub.1 ' where R.sub.1 ' is C.sub.1 -C.sub.3 alkyl, CO.sub.2 R.sub.1 ', C.sub.2 -C.sub.4 alkenyl substituted with 1-3 Cl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.5 -C.sub.6 cycloalkyl substituted with substituents selected from 1-3 CH.sub.3 or one of CH.sub.3 CH.sub.2, Cl, OCH.sub.3, C.sub.4 -C.sub.7 cycloalkylalkyl, ##STR13## where
T.sub.1 is ##STR14## or a single bond; and
T is O or NOR.sub.1.sup.III.
Japanese Patent Application No. 84-273152 (Sho 86-151188, laid open July 9, 1986) discloses the following compound ##STR15##